# Supplementary Material (ESI) for Chemical Science # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Chemical Science' _journal_coden_Cambridge 1475 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Friscic, Tomislav' _publ_contact_author_email tf253@cam.ac.uk _publ_section_title ; Solid-state dynamic combinatorial chemistry: reversibility and thermodynamic product selection in covalent mechanosynthesis ; loop_ _publ_author_name A.Belenguer T.Friscic G.Day J.Sanders # Attachment '- deposit.cif' data_1-2-new _database_code_depnum_ccdc_archive 'CCDC 796996' #TrackingRef '- deposit.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-chlorophenyl-4'-nitrophenyl disulfide ; _chemical_name_common "4-chlorophenyl-4'-nitrophenyl disulfide" _chemical_melting_point ? _chemical_formula_moiety 'C12 H8 Cl N O2 S2' _chemical_formula_sum 'C12 H8 Cl N O2 S2' _chemical_formula_weight 297.76 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.4561(3) _cell_length_b 7.1030(2) _cell_length_c 13.8346(4) _cell_angle_alpha 90.00 _cell_angle_beta 109.73(3) _cell_angle_gamma 90.00 _cell_volume 1244.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 6309 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.589 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.633 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.920 _exptl_absorpt_correction_T_max 0.988 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 8429 _diffrn_reflns_av_R_equivalents 0.0308 _diffrn_reflns_av_sigmaI/netI 0.0368 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.65 _diffrn_reflns_theta_max 27.43 _reflns_number_total 2786 _reflns_number_gt 2211 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0515P)^2^+0.1690P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2786 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0480 _refine_ls_R_factor_gt 0.0348 _refine_ls_wR_factor_ref 0.0955 _refine_ls_wR_factor_gt 0.0898 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl -0.14165(4) 0.88008(7) 0.42559(4) 0.04645(15) Uani 1 1 d . . . S1 S 0.11185(3) 0.20554(7) 0.20539(3) 0.04038(15) Uani 1 1 d . . . C1 C -0.15005(14) 0.2599(3) -0.04925(15) 0.0424(4) Uani 1 1 d . . . H1A H -0.2244 0.2610 -0.0644 0.051 Uiso 1 1 calc R . . S2 S 0.01530(4) 0.12941(7) 0.28539(4) 0.04566(16) Uani 1 1 d . . . O2 O 0.20823(13) 0.2750(3) -0.05913(13) 0.0692(5) Uani 1 1 d . . . C3 C -0.10970(15) 0.2813(3) -0.12834(15) 0.0446(5) Uani 1 1 d . . . H3A H -0.1557 0.2946 -0.1972 0.054 Uiso 1 1 calc R . . C4 C -0.09603(14) 0.6725(3) 0.38701(13) 0.0358(4) Uani 1 1 d . . . C5 C -0.16472(14) 0.5244(3) 0.35331(13) 0.0408(4) Uani 1 1 d . . . H5A H -0.2354 0.5341 0.3525 0.049 Uiso 1 1 calc R . . C6 C 0.02543(13) 0.2360(2) 0.07643(13) 0.0315(4) Uani 1 1 d . . . C7 C -0.00246(15) 0.2829(3) -0.10583(14) 0.0414(4) Uani 1 1 d . . . H7A H 0.0265 0.2987 -0.1591 0.050 Uiso 1 1 calc R . . C8 C 0.00827(14) 0.6624(3) 0.39129(13) 0.0370(4) Uani 1 1 d . . . H8A H 0.0549 0.7657 0.4154 0.044 Uiso 1 1 calc R . . C9 C -0.08434(13) 0.2369(3) 0.05140(14) 0.0372(4) Uani 1 1 d . . . H9A H -0.1142 0.2214 0.1041 0.045 Uiso 1 1 calc R . . C10 C -0.12999(15) 0.3610(3) 0.32061(14) 0.0403(4) Uani 1 1 d . . . H10A H -0.1770 0.2582 0.2964 0.048 Uiso 1 1 calc R . . C11 C 0.06345(13) 0.2616(2) -0.00526(13) 0.0338(4) Uani 1 1 d . . . O12 O 0.23699(10) 0.2693(2) 0.10312(12) 0.0588(4) Uani 1 1 d . . . C13 C 0.04256(13) 0.4972(3) 0.35938(13) 0.0376(4) Uani 1 1 d . . . H13A H 0.1139 0.4865 0.3623 0.045 Uiso 1 1 calc R . . N14 N 0.17709(12) 0.2682(2) 0.01379(13) 0.0429(4) Uani 1 1 d . . . C15 C -0.02586(14) 0.3476(3) 0.32331(12) 0.0363(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0513(3) 0.0451(3) 0.0451(3) -0.0025(2) 0.0191(2) 0.0059(2) S1 0.0364(2) 0.0484(3) 0.0315(2) -0.0009(2) 0.00502(19) 0.0068(2) C1 0.0304(9) 0.0453(12) 0.0442(10) -0.0051(8) 0.0028(8) -0.0012(8) S2 0.0658(3) 0.0357(3) 0.0382(3) 0.00361(19) 0.0212(2) 0.0041(2) O2 0.0573(9) 0.0994(14) 0.0652(10) -0.0049(9) 0.0394(8) -0.0014(9) C3 0.0447(10) 0.0445(12) 0.0342(9) -0.0021(8) -0.0005(8) 0.0008(9) C4 0.0424(9) 0.0368(10) 0.0276(8) 0.0033(7) 0.0112(7) 0.0041(8) C5 0.0364(9) 0.0468(12) 0.0382(9) 0.0029(8) 0.0113(8) -0.0004(8) C6 0.0321(8) 0.0286(9) 0.0322(8) -0.0025(7) 0.0087(7) 0.0022(7) C7 0.0498(11) 0.0403(11) 0.0342(9) -0.0026(8) 0.0146(8) -0.0012(8) C8 0.0387(9) 0.0378(10) 0.0321(9) 0.0020(7) 0.0089(7) -0.0028(8) C9 0.0313(8) 0.0422(11) 0.0376(9) -0.0033(7) 0.0109(7) -0.0024(7) C10 0.0437(10) 0.0397(11) 0.0332(9) 0.0007(8) 0.0074(8) -0.0061(8) C11 0.0330(9) 0.0320(9) 0.0360(9) -0.0039(7) 0.0110(7) 0.0009(7) O12 0.0305(7) 0.0883(12) 0.0533(9) -0.0044(8) 0.0086(7) 0.0054(7) C13 0.0360(9) 0.0418(11) 0.0342(9) 0.0030(8) 0.0107(8) 0.0015(8) N14 0.0384(8) 0.0434(9) 0.0525(10) -0.0028(7) 0.0225(8) 0.0028(7) C15 0.0476(10) 0.0346(10) 0.0259(8) 0.0037(7) 0.0114(8) 0.0010(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C4 1.7481(18) . ? S1 C6 1.7836(18) . ? S1 S2 2.0437(7) . ? C1 C3 1.384(3) . ? C1 C9 1.384(3) . ? C1 H1A 0.9500 . ? S2 C15 1.7835(19) . ? O2 N14 1.217(2) . ? C3 C7 1.370(3) . ? C3 H3A 0.9500 . ? C4 C5 1.374(3) . ? C4 C8 1.386(2) . ? C5 C10 1.383(3) . ? C5 H5A 0.9500 . ? C6 C9 1.399(2) . ? C6 C11 1.401(2) . ? C7 C11 1.383(3) . ? C7 H7A 0.9500 . ? C8 C13 1.386(3) . ? C8 H8A 0.9500 . ? C9 H9A 0.9500 . ? C10 C15 1.392(3) . ? C10 H10A 0.9500 . ? C11 N14 1.462(2) . ? O12 N14 1.226(2) . ? C13 C15 1.384(3) . ? C13 H13A 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 S1 S2 104.76(6) . . ? C3 C1 C9 121.35(17) . . ? C3 C1 H1A 119.3 . . ? C9 C1 H1A 119.3 . . ? C15 S2 S1 104.28(6) . . ? C7 C3 C1 119.05(17) . . ? C7 C3 H3A 120.5 . . ? C1 C3 H3A 120.5 . . ? C5 C4 C8 121.99(17) . . ? C5 C4 Cl1 118.95(14) . . ? C8 C4 Cl1 119.06(14) . . ? C4 C5 C10 119.39(16) . . ? C4 C5 H5A 120.3 . . ? C10 C5 H5A 120.3 . . ? C9 C6 C11 116.27(16) . . ? C9 C6 S1 121.70(13) . . ? C11 C6 S1 122.02(12) . . ? C3 C7 C11 119.76(17) . . ? C3 C7 H7A 120.1 . . ? C11 C7 H7A 120.1 . . ? C4 C8 C13 118.14(17) . . ? C4 C8 H8A 120.9 . . ? C13 C8 H8A 120.9 . . ? C1 C9 C6 120.80(17) . . ? C1 C9 H9A 119.6 . . ? C6 C9 H9A 119.6 . . ? C5 C10 C15 119.76(17) . . ? C5 C10 H10A 120.1 . . ? C15 C10 H10A 120.1 . . ? C7 C11 C6 122.75(15) . . ? C7 C11 N14 117.02(16) . . ? C6 C11 N14 120.23(15) . . ? C15 C13 C8 120.80(16) . . ? C15 C13 H13A 119.6 . . ? C8 C13 H13A 119.6 . . ? O2 N14 O12 122.81(16) . . ? O2 N14 C11 118.93(17) . . ? O12 N14 C11 118.25(15) . . ? C13 C15 C10 119.91(17) . . ? C13 C15 S2 122.57(14) . . ? C10 C15 S2 117.44(14) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 S1 S2 C15 -87.76(8) . . . . ? C9 C1 C3 C7 -1.2(3) . . . . ? C8 C4 C5 C10 -1.3(3) . . . . ? Cl1 C4 C5 C10 178.67(13) . . . . ? S2 S1 C6 C9 10.04(16) . . . . ? S2 S1 C6 C11 -170.37(13) . . . . ? C1 C3 C7 C11 0.6(3) . . . . ? C5 C4 C8 C13 0.6(3) . . . . ? Cl1 C4 C8 C13 -179.37(13) . . . . ? C3 C1 C9 C6 0.5(3) . . . . ? C11 C6 C9 C1 0.7(3) . . . . ? S1 C6 C9 C1 -179.70(14) . . . . ? C4 C5 C10 C15 0.7(3) . . . . ? C3 C7 C11 C6 0.6(3) . . . . ? C3 C7 C11 N14 -178.91(16) . . . . ? C9 C6 C11 C7 -1.3(3) . . . . ? S1 C6 C11 C7 179.11(14) . . . . ? C9 C6 C11 N14 178.27(16) . . . . ? S1 C6 C11 N14 -1.3(2) . . . . ? C4 C8 C13 C15 0.7(3) . . . . ? C7 C11 N14 O2 -6.4(3) . . . . ? C6 C11 N14 O2 174.02(17) . . . . ? C7 C11 N14 O12 172.55(17) . . . . ? C6 C11 N14 O12 -7.0(2) . . . . ? C8 C13 C15 C10 -1.2(3) . . . . ? C8 C13 C15 S2 -177.85(13) . . . . ? C5 C10 C15 C13 0.5(3) . . . . ? C5 C10 C15 S2 177.31(14) . . . . ? S1 S2 C15 C13 -41.91(15) . . . . ? S1 S2 C15 C10 141.38(12) . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 27.43 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.339 _refine_diff_density_min -0.342 _refine_diff_density_rms 0.052 data_4-4 _database_code_depnum_ccdc_archive 'CCDC 796997' #TrackingRef '- deposit.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; bis(4-methylphenyl)disulfide ; _chemical_name_common bis(4-methylphenyl)disulfide _chemical_melting_point ? _chemical_formula_moiety 'C14 H14 S2' _chemical_formula_sum 'C14 H14 S2' _chemical_formula_weight 246.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.6164(2) _cell_length_b 5.7256(2) _cell_length_c 14.7508(5) _cell_angle_alpha 90.00 _cell_angle_beta 94.881(2) _cell_angle_gamma 90.00 _cell_volume 640.93(4) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 4862 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.88 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.277 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 260 _exptl_absorpt_coefficient_mu 0.385 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.894 _exptl_absorpt_correction_T_max 0.969 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 7225 _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0406 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.69 _diffrn_reflns_theta_max 27.87 _reflns_number_total 2946 _reflns_number_gt 2494 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0350P)^2^+0.1756P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(8) _refine_ls_number_reflns 2946 _refine_ls_number_parameters 147 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0503 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.0901 _refine_ls_wR_factor_gt 0.0833 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.61718(8) 0.15117(15) 0.77455(4) 0.0577(2) Uani 1 1 d . . . C1 C 0.8333(3) 0.2114(5) 0.82617(14) 0.0400(5) Uani 1 1 d . . . C2 C 0.9773(3) 0.0665(4) 0.82082(16) 0.0420(5) Uani 1 1 d . . . H2 H 0.9651 -0.0774 0.7888 0.050 Uiso 1 1 calc R . . C3 C 1.1401(3) 0.1332(4) 0.86266(15) 0.0412(5) Uani 1 1 d . . . H3 H 1.2388 0.0333 0.8588 0.049 Uiso 1 1 calc R . . C4 C 1.1618(3) 0.3419(5) 0.90989(14) 0.0383(5) Uani 1 1 d . . . C5 C 1.0146(3) 0.4832(4) 0.91509(15) 0.0432(6) Uani 1 1 d . . . H5 H 1.0262 0.6262 0.9477 0.052 Uiso 1 1 calc R . . C6 C 0.8518(3) 0.4206(4) 0.87395(15) 0.0433(6) Uani 1 1 d . . . H6 H 0.7529 0.5199 0.8783 0.052 Uiso 1 1 calc R . . C7 C 1.3376(4) 0.4173(6) 0.95429(18) 0.0566(7) Uani 1 1 d . . . H7A H 1.4211 0.2872 0.9538 0.085 Uiso 1 1 calc R . . H7B H 1.3245 0.4640 1.0173 0.085 Uiso 1 1 calc R . . H7C H 1.3817 0.5498 0.9208 0.085 Uiso 1 1 calc R . . S2 S 0.63419(9) -0.15156(12) 0.70471(4) 0.0540(2) Uani 1 1 d . . . C8 C 0.6976(3) -0.0701(4) 0.59541(14) 0.0341(5) Uani 1 1 d . . . C9 C 0.6590(3) -0.2289(4) 0.52577(16) 0.0375(5) Uani 1 1 d . . . H9 H 0.6004 -0.3708 0.5374 0.045 Uiso 1 1 calc R . . C10 C 0.7059(3) -0.1807(4) 0.43939(15) 0.0386(5) Uani 1 1 d . . . H10 H 0.6801 -0.2914 0.3922 0.046 Uiso 1 1 calc R . . C11 C 0.7903(3) 0.0269(4) 0.42003(15) 0.0348(5) Uani 1 1 d . . . C12 C 0.8289(3) 0.1831(4) 0.49096(14) 0.0356(5) Uani 1 1 d . . . H12 H 0.8872 0.3252 0.4793 0.043 Uiso 1 1 calc R . . C13 C 0.7843(3) 0.1366(4) 0.57841(14) 0.0352(5) Uani 1 1 d . . . H13 H 0.8128 0.2451 0.6261 0.042 Uiso 1 1 calc R . . C14 C 0.8401(4) 0.0812(6) 0.32562(17) 0.0550(7) Uani 1 1 d . . . H14A H 0.7680 0.2111 0.3002 0.083 Uiso 1 1 calc R . . H14B H 0.8198 -0.0568 0.2868 0.083 Uiso 1 1 calc R . . H14C H 0.9649 0.1247 0.3284 0.083 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0362(3) 0.0977(6) 0.0390(3) -0.0078(4) 0.0025(2) 0.0032(3) C1 0.0372(11) 0.0585(16) 0.0245(10) 0.0017(10) 0.0049(8) 0.0040(11) C2 0.0443(12) 0.0438(13) 0.0382(12) -0.0065(10) 0.0055(9) -0.0005(11) C3 0.0402(11) 0.0429(13) 0.0409(12) -0.0042(11) 0.0055(9) 0.0077(11) C4 0.0428(12) 0.0437(12) 0.0290(10) 0.0040(11) 0.0070(9) -0.0009(11) C5 0.0569(14) 0.0412(14) 0.0322(11) -0.0016(10) 0.0072(10) 0.0009(11) C6 0.0473(13) 0.0459(14) 0.0378(12) 0.0032(10) 0.0102(10) 0.0117(11) C7 0.0497(14) 0.0652(19) 0.0544(16) -0.0114(14) 0.0016(12) -0.0071(13) S2 0.0552(4) 0.0659(4) 0.0397(3) 0.0117(3) -0.0033(3) -0.0236(3) C8 0.0300(10) 0.0358(11) 0.0356(11) 0.0039(9) -0.0028(8) -0.0036(9) C9 0.0318(10) 0.0287(11) 0.0503(14) -0.0004(9) -0.0060(9) -0.0024(9) C10 0.0369(11) 0.0359(13) 0.0417(12) -0.0111(10) -0.0037(9) 0.0048(10) C11 0.0284(10) 0.0381(12) 0.0377(11) -0.0009(10) 0.0014(9) 0.0056(9) C12 0.0321(10) 0.0322(11) 0.0424(12) 0.0033(10) 0.0019(8) -0.0026(9) C13 0.0353(10) 0.0318(11) 0.0377(11) -0.0059(10) -0.0026(8) -0.0069(9) C14 0.0543(14) 0.071(2) 0.0410(13) 0.0000(13) 0.0121(11) 0.0089(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C1 1.788(2) . ? S1 S2 2.0261(11) . ? C1 C2 1.383(3) . ? C1 C6 1.391(4) . ? C2 C3 1.391(3) . ? C2 H2 0.9500 . ? C3 C4 1.386(3) . ? C3 H3 0.9500 . ? C4 C5 1.390(3) . ? C4 C7 1.502(3) . ? C5 C6 1.380(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? S2 C8 1.784(2) . ? C8 C9 1.385(3) . ? C8 C13 1.388(3) . ? C9 C10 1.380(3) . ? C9 H9 0.9500 . ? C10 C11 1.392(3) . ? C10 H10 0.9500 . ? C11 C12 1.389(3) . ? C11 C14 1.507(3) . ? C12 C13 1.387(3) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 S1 S2 106.58(9) . . ? C2 C1 C6 119.9(2) . . ? C2 C1 S1 124.46(19) . . ? C6 C1 S1 115.59(18) . . ? C1 C2 C3 119.4(2) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C4 C3 C2 121.6(2) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C3 C4 C5 117.8(2) . . ? C3 C4 C7 122.0(2) . . ? C5 C4 C7 120.1(2) . . ? C6 C5 C4 121.5(2) . . ? C6 C5 H5 119.2 . . ? C4 C5 H5 119.2 . . ? C5 C6 C1 119.7(2) . . ? C5 C6 H6 120.2 . . ? C1 C6 H6 120.2 . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C8 S2 S1 105.64(8) . . ? C9 C8 C13 120.0(2) . . ? C9 C8 S2 116.23(17) . . ? C13 C8 S2 123.76(17) . . ? C10 C9 C8 119.9(2) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C9 C10 C11 121.4(2) . . ? C9 C10 H10 119.3 . . ? C11 C10 H10 119.3 . . ? C12 C11 C10 117.8(2) . . ? C12 C11 C14 120.6(2) . . ? C10 C11 C14 121.5(2) . . ? C13 C12 C11 121.6(2) . . ? C13 C12 H12 119.2 . . ? C11 C12 H12 119.2 . . ? C12 C13 C8 119.3(2) . . ? C12 C13 H13 120.4 . . ? C8 C13 H13 120.4 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.178 _refine_diff_density_min -0.272 _refine_diff_density_rms 0.040